Kenny is the only person this century to win his debut in the Halloween Foosball Tournament. In 2000, Kenny beat Gina in the first round of the Halloween Foosball Tournament. He had been scheduled to face Angel, however when Angel wanted to face Corey in the first round, Kenny's opponent was switched with Corey's original opponent. The victory over Gina set off a long rivalry between the two, culminating with Gina being the losing scorekeeper in the 2001 finals, while Kenny was the winning scorekeeper. Kenny lost in the second round of the 2000 tournament to Jim.
The next two years saw Kenny lose in the first round of the HFT, both times again against one of the Ouellettes. In 2001, Keith beat Kenny 5-1. In 2002, Keith won by a count of 5-something
2002 also saw a decision that would lead to Kenny's crowning moment however. In a shocking turn of events, Kenny and Gina put their past differences behind them and surprisingly entered the doubles tournament as a team. Kenny continued his apparent war on the Ouellette family, but this time with one of their own on his side. Kenny and Gina came within a single goal of pulling off the biggest upset in years when they just barely lost to Greg and Keith. In 2003, the same two teams would once again face in the first round of the doubles tournament and in one of the most stunning upsets of all time, Kenny and Gina won. The two would make it all the way to the finals where they would finally fall in a close and competitive game with another surprising team, Nick and Kyle.
Kenny actually beat Shawn in the first round of the 2003 Singles tournament as well, 6-4, however he had to leave, meaning that Shawn would take his place in the semi-finals. Kenny is still given credit for the win over Shawn however and thus went 1-0 in 2003 to improve his record to 2-3.
